Ethyl diazoacetate → Ethyl Spiro[2.5]octane-1-carboxylate

HRID 2079460Notes

Reaction equation

HRID 2079460 reaction equation
[CH2:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>[Cu].CC1CCCCC1>[CH:10]1([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]2([CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)[CH2:1]1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 14502Methylenecyclohexane

Product 1

HCID 11206164Ethyl Spiro[2.5]octane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7962MethylcyclohexaneSolvent

Conditions

Temperature
102.5 °C

Procedure

A 250 mL round-bottom flask was charged with methylenecyclohexane (20.0 g, 0.21 mol, commercially available from Aldrich), copper powder (2.8 g), methyl cyclohexane (50 mL) and heated to 105° C. Ethyl diazoacetate (26 g, 0.23 mol, commercially available from Aldrich) was added dropwise over an 8-hour period while maintaining the temperature between 100-105° C. Upon complete addition, the mixture was heated an additional 2 hours, allowed to cool to ambient temperature and stirred for an additional 12 hours. The reaction mixture was filtered and concentrated under reduced pressure to afford the title compound which was used without further purification.

Workup

  1. additionUpon complete addition
  2. temperaturethe mixture was heated an additional 2 hours
  3. temperatureto cool to ambient temperature
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-31fec05fb9114d65983c9527a15153e1
Source dataset
uspto-grants-2011_04
Patent number
US07932245B2

Reaction notes

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